The music player works as intended, some songs just have a few seconds of silence at the start before they start playing. You need to wait for the songs to start playing before clicking to the next song.
And the dialogue at the start of each day was coded to repeat so I wouldn't have to write 30 unique interactions for each day. There are some shorter, more generic dialogues which were set to appear more freqently, and some slightly longer dialogues which were coded to appear less frequently. It's possible to get the same dialogue multiple times in one playthrough, but it's not a bug.